Guaiacol carbonate sulfo-acid derivative.



, tains to nake anduse the same.

. 2111110311, '01 Munro 1 RINGER so To' alto/7 0m it may concern:

'Beit known that I, ALF ED EINHORN, citizen-of Germany, residing at Munich, Ba-

varia, Gern any, have invented certain new and useful Improvements in the Art of Making Guaiacol- Carbonate Sulforcid Derivatives; and do'hereby declare the follow ng to be a full, clear, and exact description of the invention, such as will enable others. skilled in the art to which it apper- This invention relates to the manufacture of guaiacol sulfo-acid derivatives and in particular to", the preparation of the salts of the sulfo-acids of gruaiacol carbonate.

a .The objects of the invention are to obtain .such salts of this character as are adapted .for therapeutic purposes, and which can be used together Withferric preparations with-- out inconvenience, producing no color reactions with them as is the case with guaiacol sulfo-acidsalts, and which, moreover, are more pleasant to the taste than the latter.

Viththese objects in view my invention consists in the class of compounds hereinafter described-and claimed and also in the process for making them as hereinafter dey ammonia, they are obviously not what th'ey have beensupposed'to be, but belong rather scribed and covered in the claims.

I have found-that the salts of the ninnoanddi-sulfo acids of guaiacol carbonate,

which are soluble inv water are formed when phosgen acts upon gualacol sulfo acids or known substitutes, as. for instance. bases of pyridin etc., according ,to the following formulae i QH d o -coo err nt-0on ooon=o nroon omoo.m+2no1 Up to now it has not been possible to proderivatives of the Specification (if-Letters Patent.-

inixtures of several salts.

not, when-"heated STATES PATENT OFF CE H, GERMANYWASSIGNQR TO THE FIRM. or o. jl isoim- OFYNIEDER'. INV'GELHEIM, ERMANY.

GUAIlACOL CARBONATE SULFO-ACID DERIVATIVE.

Patented 0a. 26, 1909.

Application filed June 22, 1908. Serial No. 439,842.

and tetrasali'cylid are formed from salicylic acid. but in no case the'carbonate of salicylic acid. In cooperation With Gustav Haas (Bcrz'chts dcr De-utshe'n' Ohe-mischcn GcseZZ- s(:/Laft,.vol. 38, page 3627,- see also his dissertation, Munich 1905, pages 15 and 30) it was pointed out that salicylic acid is not acted upon at all by alkali carbonates or hydrates. It was therefore to be expected that the-sulfoacids of guaiacol would, when treated withphosgen, behave similarly to salicylic acid, and it could not be foreseen that the very reverse would take place, and that they are capable of forming carbonates, in spite of the-acid sulfo group.

Salts of the sulfo acids of guaiacol carbonate have heretofore remained unknown. In the German patent specification No. 91078 salts of the sulfo acids of the aliphatic creosote ester are described. These, howeven'are in no way uniforn'i. and are most probably Sincethey give a color reaction when treated with ferric chlorid, and separatet-he sulfo group when heated with caustic solutions. and further change to amino, dcrivatcs when treated with to a totally different class of combinations reaction with ferric chlorid and which do with annnonia and caustic solut.ions,'separate the sulfo group.

The salts of the sulfo acids of guaiacol carbonate are intermediate between the. two preparations of guaiacol inostused for medicinal purposes, namely, the guaiacol carbonate and the ,g'uaiacol sulfo acid salts (for instance. thiocol); In cont ardistinction to guaiacol"carbonate they have the advantage of being easily soluble in water, ,aiid-coinpared with t-hiocol they taste better and give no color reaction with ferric salts and can reparations for medicinal purposes. Example I: Phosgen is passed into a cooled solution consist ng of 5 grams of the potassium salt of guaiacol sulfo acid (thiocol) and 3 grams ofcaustic potash i112? grams of water, until an acid reaction is shown; hereby the greater mass of the potassium salt of guaiacol carbonate disulfo acid is directly precipitated, and the remainder can phosgen in the presence of Cit . therefore be used in combination with ferric be separated from thefiltered solution with chlorid of potassium. The potassium salt of guaiacol carbonate di-sulfo acid crystallizes out-of a watery solution, and it gives no color reaction with zferricchlorid, and does. not reduce silver nitrate solutions, whereby it is distinguished from the potassium salt of guaiacol sulfo'acid (thiocol). From diluted alcohol. it-separates in fthe 'form of needles; in methyhc alcohol it is only very slightly soluble and .in." eth'yli'c alcohol quite insoluble: Neither hydrochloric acid nor sulfuric acid" alter the. concentrated watery solution f th Salt- Example II: Phosgen 1s'passedintoja cooled solution consisting of grams of the potassium salt of guaiacolsulfo acid (thiocol) and 10.4 grams of guaiacol in -L20 sium salt 'of guaiacol. carbonate mono-sulfo from methylic alcohol, in which it is only acid separates in the form of crystals, and finally, when alcohol is added to the filtered solution, the otassium sa t of guaia'col carbonate disul 0 acid is pr cipitated.

For purifying, the potassium salt of aiacolcarbonate mono-sulfo acid is 'c stallized out of a watery solution, from which it separates in the form of fatty, lustrous,

prismatic crystals; with ferric chlorid' it 'ves no color reaction; from diluted alcohol, m'which it dissolves'with difliculty, it crystallizes in the form of small lustrous needles;

with difficulty soluble, it separates in the form of long needles, and from absolutealc'ohol, in which it is only soluble with the greatest difliculty, it separates as microscopic indistinct crystals. An addition of hydrochloric acid or sulfuric acid to a concentrated solution of the salt produces no change.

The products obtained by this process are.

to be used for therapeutic purposes.

What I claim as my invention and desire to secure by Letters Patent, is:

1. The process for the roduction of salt LoUIs F. MUELLER,

'of guaiacol carbonate sul o-acids, which consists 1n causing phosgen to react on an alkaeasily soluble inwater and line bath containing the potassium salt of 'guaiacol sulfo-acid until the bath reacts acid.

'2. The process for the production of a salt" of guaiaeol carbonate sulfo-acids, which consists in passing phosgen into a cooled aqueous bath of a salt of aiacol sulfo-acid tog 'etherwith an alkali, until the bathreacts ac1d.. Y

3. The process for the production of asalt ofjguaiacol carbonate sulfo-acids, which con sists in passing hosgen into a' cooled aqueaiacol s'ulfo-acid toa of guaiacol carbonate sul o-a'cid's, which consists in passing phosgen into acooled aqueous bath of a'salt ofjguaicol sulfo-acid together "with an alkali, nntilthe bathreacts acid,

then separating the resulting precipitate and. finally treating the remainder of the bath" with potassium chlorid.

s a. new chemicalcompound, a salt ofa sulfo-acid of .guaiacol-carbonate, having the following properties 2-- It is easily soluble in waterand gives no color react-ion with ferric salts and, when heated with ammonia or with caustic alkali solution, does not split oil the sulfo-group.

6. As a new chemical compound, an alkali" metal salt of a sulfo-acid of guaiacol-car- 'bonate which has the properties of being reaction with ferric saltsan when heated with ammonia .or with caustic alkali solution, does not split ofi the sulfo-group.

7 As a new chemical compound the potassium salt. of the :disulfo-aicid of guaiacol: carbonate, which crystallizes out of water .and dilute alcohol, which crystallizes out of the latter in the form'of pointed needles, is

thebath with a halogen salt of an alkali... '4. The process for the roduction'of a salt giving no color only slightly soluble in methyl-alcohol and insoluble in concentrated ethyl-alcohol, which gives no color reaction with ferric salts and which is not altered by dilute mineral acids but is altered by alkalies.

In testimony whereof. I hereunto aflix my ALFRED EINHORN. Witnesses MATHILDE K. HELD.

signature in the presence of two witnesses; 

